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Instructional leadership theory urges principals to spend time observing classroom instruction. However, little is known about what predicts the extent to which principals participate in this behavior. This paper analyzes a subsample of the 2013 Teaching and Learning International Survey (TALIS) using multilevel mixed-effects ordered logistic models to examine principals’ rates of classroom observations. Using a sample of 4,950 principals from 25 countries, this study finds a significant relationship between higher frequencies of principal-reported continued professional development throughout the year and higher categories of principal reported classroom observations. These findings support instructional leadership theory and suggest that continued professional development can help explain differences in the rate that principals report spending inside teacher’s classrooms.